US6787629B2 - Dental resin materials, method of manufacture, and uses thereof - Google Patents
Dental resin materials, method of manufacture, and uses thereof Download PDFInfo
- Publication number
- US6787629B2 US6787629B2 US10/287,428 US28742802A US6787629B2 US 6787629 B2 US6787629 B2 US 6787629B2 US 28742802 A US28742802 A US 28742802A US 6787629 B2 US6787629 B2 US 6787629B2
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- US
- United States
- Prior art keywords
- resin composition
- filler
- percent
- weight
- equal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime, expires
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- 0 *C(=C)C(=O)OCCC(COC1=CC=C(CC2=CC=C(OCC(CCOC(=O)C(*)=C)OC(=O)COC(C)=O)C=C2)C=C1)OC Chemical compound *C(=C)C(=O)OCCC(COC1=CC=C(CC2=CC=C(OCC(CCOC(=O)C(*)=C)OC(=O)COC(C)=O)C=C2)C=C1)OC 0.000 description 8
- XUCHXOAWJMEFLF-UHFFFAOYSA-N C1=CC(OCC2CO2)=CC=C1CC1=CC=C(OCC2CO2)C=C1 Chemical compound C1=CC(OCC2CO2)=CC=C1CC1=CC=C(OCC2CO2)C=C1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/045—Aromatic polycarbonates containing aliphatic unsaturation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2991—Coated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2991—Coated
- Y10T428/2993—Silicic or refractory material containing [e.g., tungsten oxide, glass, cement, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2991—Coated
- Y10T428/2993—Silicic or refractory material containing [e.g., tungsten oxide, glass, cement, etc.]
- Y10T428/2995—Silane, siloxane or silicone coating
Abstract
Description
TABLE 1 | |||||
Water | |||||
Absorption | Double Bond | ||||
Molecular | Refractive | (microgram/ | Shrinkage | Conversion | |
Resin | Weight | Index | mm3/week) | (percent) | (percent) |
Bis- | 500 | 1.5557 | 35 | 4.44 | 40 |
GMA | |||||
PCBis- | 2,000 | 1.5315 | 20 | 3.49 | 36 |
GMA | |||||
TABLE 2 | |||
Water absorption | |||
(microgram/mm3/ | Weight loss | ||
Resin | Flexural strength (psi) | week) | (g/mm3/week) |
Resin 1 | 16445 (810) | 11 | 3.4 |
|
13837 (2138) | 10 | 4.2 |
*Comparative Example |
TABLE 3 | ||
Sample | Paste 1 | |
Flexural Strength (psi) | 19844 (1025) | 18700 (2086) |
Depth of cure (mm) | 4.318 | 5.0 |
|
80/65 | 82/72 |
(top/bottom) | ||
TABLE 4 | |
Components | Wt. percent |
PCBisGMA | 5.10 |
BisGMA | 7.45 |
UDMA | 5.72 |
HDDMA | 5.61 |
BHT | 0.005 |
UV-5411 | 0.20 |
Camphorquinone | 0.05 |
EDMAB | 0.11 |
Lucirin TPO | 0.05 |
UVITEX-OB | 0.005 |
Barium zirconium silicate* | 32.0 |
Barium borosilicate | 36.0 |
Silica | 4.6 |
Methacryloxysilane | 3.0 |
FD&C pigments: Y #5, |
<0.1 |
*The barium zirconate silicate is a nanohybrid filler made in accordance with Example 8 below (Powder 2). |
TABLE 5 | ||
Generalized Wear |
Materials | Surface | Marginal | Localized wear |
PCBisGMA Composition | 3.8 ± 1.0 | 11.2 ± 3.5 | 47.4 ± 16.1 |
Z250 | 9.8 ± 0.6 | 17.6 ± 3.4 | 52.9 ± 19.3 |
Esthet-X ® | 13.1 ± 5.8 | 13.1 ± 3.6 | 49.8 ± 13.4 |
Claims (20)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/287,428 US6787629B2 (en) | 2001-11-02 | 2002-11-04 | Dental resin materials, method of manufacture, and uses thereof |
US10/683,750 US7670580B2 (en) | 2001-11-02 | 2003-10-10 | Dental resin materials, method of manufacture, and uses thereof |
US11/151,723 US7589132B2 (en) | 2001-05-01 | 2005-06-13 | Dental resins, dental composite materials, and method of manufacture thereof |
US11/289,758 US7470728B2 (en) | 2001-05-01 | 2005-11-29 | Dental glazes and method of manufacture and use thereof |
US12/697,585 US9296891B2 (en) | 2001-11-02 | 2010-02-01 | Dental resin materials, method of manufacture, and uses thereof |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US33688301P | 2001-11-02 | 2001-11-02 | |
US35925202P | 2002-02-20 | 2002-02-20 | |
US37613802P | 2002-04-29 | 2002-04-29 | |
US10/287,428 US6787629B2 (en) | 2001-11-02 | 2002-11-04 | Dental resin materials, method of manufacture, and uses thereof |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/136,031 Continuation-In-Part US6653365B2 (en) | 2001-05-01 | 2002-04-30 | Dental composite materials and method of manufacture thereof |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/683,750 Division US7670580B2 (en) | 2001-05-01 | 2003-10-10 | Dental resin materials, method of manufacture, and uses thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
US20030125444A1 US20030125444A1 (en) | 2003-07-03 |
US6787629B2 true US6787629B2 (en) | 2004-09-07 |
Family
ID=27501461
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/287,428 Expired - Lifetime US6787629B2 (en) | 2001-05-01 | 2002-11-04 | Dental resin materials, method of manufacture, and uses thereof |
US10/683,750 Active 2024-10-16 US7670580B2 (en) | 2001-05-01 | 2003-10-10 | Dental resin materials, method of manufacture, and uses thereof |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/683,750 Active 2024-10-16 US7670580B2 (en) | 2001-05-01 | 2003-10-10 | Dental resin materials, method of manufacture, and uses thereof |
Country Status (1)
Country | Link |
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US (2) | US6787629B2 (en) |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040086446A1 (en) * | 2001-11-02 | 2004-05-06 | Weitao Jia | Dental resin materials, method of manufacture, and uses thereof |
US20050186527A1 (en) * | 2004-02-19 | 2005-08-25 | Pameijer Cornelis H. | Device for determining shades of dental restorations |
US20060058415A1 (en) * | 2004-09-14 | 2006-03-16 | Arthur Samuel D | Materials leading to improved dental composites and dental composites made therefrom |
US20060058418A1 (en) * | 2004-09-14 | 2006-03-16 | Brandenburg Charles J | Materials leading to improved dental composites and dental composites made therefrom |
US20060058414A1 (en) * | 2004-09-14 | 2006-03-16 | Arthur Samuel D | Materials leading to improved dental composites and dental composites made therefrom |
US20060058416A1 (en) * | 2004-09-14 | 2006-03-16 | Brandenburg Charles J | Materials leading to improved dental composites and dental composites made therefrom |
US20060241205A1 (en) * | 2005-04-20 | 2006-10-26 | Weitao Jia | Filler materials for dental composites |
US20070015845A1 (en) * | 2005-07-15 | 2007-01-18 | Pentron Clinical Technologies, Llc | Dental resin composition, method of manufacture, and method of use thereof |
US20080145820A1 (en) * | 2003-05-08 | 2008-06-19 | Ajit Karmaker | Method of manufacturing high strength dental restorations |
US20080206712A1 (en) * | 2007-02-28 | 2008-08-28 | Ultradent Products, Inc. | Resin reinforced zinc polycarboxylate temporary cement compositions and related kits and methods |
US20090030109A1 (en) * | 2005-11-18 | 2009-01-29 | Hare Robert V | Dental composite restorative material |
US20090047634A1 (en) * | 2001-12-28 | 2009-02-19 | Randall Rex Calvert | Apparatus and method for root canal obturation |
US20090191505A1 (en) * | 2008-01-29 | 2009-07-30 | Clark David J | Dental Matrix Devices Specific To Anterior Teeth, and Injection Molded Filling Techniques and Devices |
US20100158960A1 (en) * | 2008-12-18 | 2010-06-24 | Dinesh Chandra | Porous polymer coating for tooth whitening |
EP2230286A1 (en) | 2009-03-20 | 2010-09-22 | Pentron Clinical Technologies, LLC | Dental resin composition, method of manufacture, and method uf use thereof |
EP2253301A1 (en) | 2009-05-18 | 2010-11-24 | Pentron Clinical Technologies, LLC | Pre-treated acid-reactive fillers and their use in dental applications |
WO2010144787A1 (en) | 2009-06-11 | 2010-12-16 | Pentron Clinical Technologies, Llc | Epoxy-containing composition curable by multiple polymerization mechanisms |
US20100323330A1 (en) * | 2005-11-29 | 2010-12-23 | Pentron Clinical Technologies Llc | Tooth Colorant and Whitener, Method of Manufacture, and Method of Use Thereof |
US20100330582A1 (en) * | 2006-06-08 | 2010-12-30 | The University Of Tokushima | Method for production of novel nano silica particle and use of the nano silica particle |
EP2537507A2 (en) | 2011-06-20 | 2012-12-26 | Kerr Corporation | Compositions dentaires contenant des fibres raccourcies |
US8342351B2 (en) | 2007-08-03 | 2013-01-01 | Terry J. Hobbs, SR. | Cap for caulking cartridge or similar container |
US8735463B2 (en) | 2007-05-31 | 2014-05-27 | Creighton University | Self-healing dental composites and related methods |
CN110550545A (en) * | 2019-07-15 | 2019-12-10 | 广东中烟工业有限责任公司 | Guide rail and guide wheel device with high wear resistance |
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US7709029B2 (en) * | 2001-01-24 | 2010-05-04 | Ada Foundation | Calcium-containing restoration materials |
US9296891B2 (en) * | 2001-11-02 | 2016-03-29 | Pentron Clinical Technologies, Llc | Dental resin materials, method of manufacture, and uses thereof |
US20040241609A1 (en) * | 2003-05-08 | 2004-12-02 | Weitao Jia | Method of manufacturing high strength dental restorations |
US7104322B2 (en) * | 2003-05-20 | 2006-09-12 | Weatherford/Lamb, Inc. | Open hole anchor and associated method |
US7700667B2 (en) * | 2004-01-29 | 2010-04-20 | Pentron Clinical Technologies, Llc | Dental resin composition, method of manufacture, and method of use thereof |
US20060058417A1 (en) * | 2004-09-14 | 2006-03-16 | Brandenburg Charles J | Materials leading to improved dental composites and dental composites made therefrom |
US7560500B2 (en) * | 2005-05-13 | 2009-07-14 | E. I. Du Pont De Nemours And Company | Materials leading to improved dental composites and dental composites made therefrom |
US8084514B2 (en) | 2005-05-13 | 2011-12-27 | E. I. Du Pont De Nemours And Company | Materials leading to improved dental composites and dental composites made therefrom |
US20060270752A1 (en) * | 2005-05-26 | 2006-11-30 | Ada Foundation | Dental releasing materials |
US20070123604A1 (en) * | 2005-05-26 | 2007-05-31 | Ada Foundation | Dental releasing materials |
US7748601B2 (en) * | 2005-09-28 | 2010-07-06 | General Electric Company | Brazed articles, braze assemblies and methods therefor utilizing gold/copper/nickel brazing alloys |
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US20080200587A1 (en) * | 2007-02-16 | 2008-08-21 | 3M Innovative Properties Company | Pressure-sensitive adhesive containing acicular silica particles crosslinked with polyfunctional aziridines |
US20080196627A1 (en) * | 2007-02-16 | 2008-08-21 | Core Technologies, Inc. | Vitreous enamel coating powder |
US8298664B2 (en) * | 2007-04-12 | 2012-10-30 | Pentron Clinical Technologies, Llc | Fiber-reinforced composite dental materials and method of manufacture |
DE102012006152A1 (en) * | 2012-03-28 | 2013-10-02 | Heraeus Kulzer Gmbh | Polymerized dental composites with improved performance properties, methods for adjusting the performance of polymerisable dental composites, and dental composites optimized by these methods |
Citations (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3066112A (en) | 1959-01-30 | 1962-11-27 | Rafael L Bowen | Dental filling material comprising vinyl silane treated fused silica and a binder consisting of the reaction product of bis phenol and glycidyl acrylate |
US3179623A (en) | 1959-01-30 | 1965-04-20 | Rafael L Bowen | Method of preparing a monomer having phenoxy and methacrylate groups linked by hydroxy glyceryl groups |
US3751399A (en) | 1971-05-24 | 1973-08-07 | Lee Pharmaceuticals | Polyacrylate resin compositions |
US3755420A (en) | 1972-07-14 | 1973-08-28 | Lee Pharmaceuticals | Triglycidyl ether of trihydroxy bisphenyl ester of acrylic acid |
US3926906A (en) | 1968-06-14 | 1975-12-16 | Johnson & Johnson | Dental filling package |
US4306913A (en) | 1978-09-11 | 1981-12-22 | American Dental Association Health Foundation | Method for preparing microporous glassy filler grains for dental resin composites |
US4503169A (en) | 1984-04-19 | 1985-03-05 | Minnesota Mining And Manufacturing Company | Radiopaque, low visual opacity dental composites containing non-vitreous microparticles |
US4544359A (en) | 1984-01-13 | 1985-10-01 | Pentron Corporation | Dental restorative material |
US4547531A (en) | 1984-08-02 | 1985-10-15 | Pentron Corporation | Two component (paste-paste) self-curing dental restorative material |
US4764497A (en) | 1981-12-23 | 1988-08-16 | Tokuyama Soda Kabushiki Kaisha | Amorphous, spherical inorganic compound and process for preparation thereof |
US5276068A (en) * | 1985-03-29 | 1994-01-04 | Jeneric/Pentron, Inc. | Dental resin materials |
US5707440A (en) | 1993-10-07 | 1998-01-13 | Heraeus Kulzer Gmbh | Inorganic filler material with retention properties, and method and use of such material |
US5726068A (en) | 1996-01-24 | 1998-03-10 | The United States Of America As Represented By The Secretary Of The Army | Diffusive sampler system for determining chemical vapor levels |
US5861445A (en) | 1997-05-08 | 1999-01-19 | American Dental Association Health Foundation | Reinforcement of dental and other composite materials |
US5865623A (en) | 1997-03-12 | 1999-02-02 | Bisco, Inc. | Flexible dental composite compositions and restorative methods using flexible dental compositions |
US5876210A (en) | 1994-04-22 | 1999-03-02 | Dentsply G.M.B.H. | Dental polymer product |
US5936006A (en) | 1996-04-26 | 1999-08-10 | Ivoclar Ag | Filled and polymerizable dental material |
US5969000A (en) | 1997-01-17 | 1999-10-19 | Jeneric Pentron Incorporated | Dental resin materials |
US6013694A (en) * | 1997-10-16 | 2000-01-11 | Jeneric/Pentron Incorporated | Dental composites comprising ground, densified, embrittled glass fiber filler |
US6232367B1 (en) | 1999-10-07 | 2001-05-15 | Kerr Corporation | Opalescent fillers for dental restorative composites |
US6270562B1 (en) | 1998-06-11 | 2001-08-07 | Jeneric/Pentron, Inc. | Filler material for dental composites |
US6362251B1 (en) | 1998-10-09 | 2002-03-26 | Degussa-Huls Aktiengesellschaft | Dental material comprising porous glass ceramics, porous glass ceramics, processes and use |
US6387981B1 (en) | 1999-10-28 | 2002-05-14 | 3M Innovative Properties Company | Radiopaque dental materials with nano-sized particles |
US6417246B1 (en) | 1999-09-21 | 2002-07-09 | Jenerica/Pentron Incorporated | Dental composite materials |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4224023A (en) * | 1976-08-16 | 1980-09-23 | Pennwalt Corporation | Dental restorative kit and method of restoring tooth structure |
US4180911A (en) * | 1977-09-16 | 1980-01-01 | Applied Science Corporation | Method for direct bonding of orthodontic structures to teeth using flouride pretreatment |
JPS604561A (en) * | 1983-06-23 | 1985-01-11 | Tokuyama Soda Co Ltd | Surface-treated oxide |
US5856373A (en) * | 1994-10-31 | 1999-01-05 | Minnesota Mining And Manufacturing Company | Dental visible light curable epoxy system with enhanced depth of cure |
US5580655A (en) * | 1995-03-03 | 1996-12-03 | Dow Corning Corporation | Silica nanoparticles |
US6193792B1 (en) * | 1999-04-28 | 2001-02-27 | Xerox Corporation | Ink compositions for ink jet printing |
US6730156B1 (en) * | 1999-10-28 | 2004-05-04 | 3M Innovative Properties Company | Clustered particle dental fillers |
CA2423597A1 (en) * | 2000-10-16 | 2002-04-25 | 3M Innovative Properties Company | Method of making ceramic aggregate particles |
US6586483B2 (en) * | 2001-01-08 | 2003-07-01 | 3M Innovative Properties Company | Foam including surface-modified nanoparticles |
US6787629B2 (en) * | 2001-11-02 | 2004-09-07 | Pentron Clinical Technologies, Llc | Dental resin materials, method of manufacture, and uses thereof |
US6653365B2 (en) * | 2001-05-01 | 2003-11-25 | Pentron Clinical Technologies, Llc | Dental composite materials and method of manufacture thereof |
US6889948B2 (en) * | 2001-12-06 | 2005-05-10 | Malcom R. Melancon | Flange for connecting fan to manway |
-
2002
- 2002-11-04 US US10/287,428 patent/US6787629B2/en not_active Expired - Lifetime
-
2003
- 2003-10-10 US US10/683,750 patent/US7670580B2/en active Active
Patent Citations (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3066112A (en) | 1959-01-30 | 1962-11-27 | Rafael L Bowen | Dental filling material comprising vinyl silane treated fused silica and a binder consisting of the reaction product of bis phenol and glycidyl acrylate |
US3179623A (en) | 1959-01-30 | 1965-04-20 | Rafael L Bowen | Method of preparing a monomer having phenoxy and methacrylate groups linked by hydroxy glyceryl groups |
US3194784A (en) | 1959-01-30 | 1965-07-13 | Rafael L Bowen | Silica-resin direct filling material and method of preparation |
US3926906A (en) | 1968-06-14 | 1975-12-16 | Johnson & Johnson | Dental filling package |
US3751399A (en) | 1971-05-24 | 1973-08-07 | Lee Pharmaceuticals | Polyacrylate resin compositions |
US3755420A (en) | 1972-07-14 | 1973-08-28 | Lee Pharmaceuticals | Triglycidyl ether of trihydroxy bisphenyl ester of acrylic acid |
US4306913A (en) | 1978-09-11 | 1981-12-22 | American Dental Association Health Foundation | Method for preparing microporous glassy filler grains for dental resin composites |
US4764497A (en) | 1981-12-23 | 1988-08-16 | Tokuyama Soda Kabushiki Kaisha | Amorphous, spherical inorganic compound and process for preparation thereof |
US4544359A (en) | 1984-01-13 | 1985-10-01 | Pentron Corporation | Dental restorative material |
US4503169A (en) | 1984-04-19 | 1985-03-05 | Minnesota Mining And Manufacturing Company | Radiopaque, low visual opacity dental composites containing non-vitreous microparticles |
US4547531A (en) | 1984-08-02 | 1985-10-15 | Pentron Corporation | Two component (paste-paste) self-curing dental restorative material |
US5444104A (en) * | 1985-03-29 | 1995-08-22 | Jeneric/Pentron, Inc. | Dental resin materials |
US5276068A (en) * | 1985-03-29 | 1994-01-04 | Jeneric/Pentron, Inc. | Dental resin materials |
US5707440A (en) | 1993-10-07 | 1998-01-13 | Heraeus Kulzer Gmbh | Inorganic filler material with retention properties, and method and use of such material |
US5876210A (en) | 1994-04-22 | 1999-03-02 | Dentsply G.M.B.H. | Dental polymer product |
US5726068A (en) | 1996-01-24 | 1998-03-10 | The United States Of America As Represented By The Secretary Of The Army | Diffusive sampler system for determining chemical vapor levels |
US5936006A (en) | 1996-04-26 | 1999-08-10 | Ivoclar Ag | Filled and polymerizable dental material |
US5969000A (en) | 1997-01-17 | 1999-10-19 | Jeneric Pentron Incorporated | Dental resin materials |
US5865623A (en) | 1997-03-12 | 1999-02-02 | Bisco, Inc. | Flexible dental composite compositions and restorative methods using flexible dental compositions |
US5861445A (en) | 1997-05-08 | 1999-01-19 | American Dental Association Health Foundation | Reinforcement of dental and other composite materials |
US6013694A (en) * | 1997-10-16 | 2000-01-11 | Jeneric/Pentron Incorporated | Dental composites comprising ground, densified, embrittled glass fiber filler |
US6270562B1 (en) | 1998-06-11 | 2001-08-07 | Jeneric/Pentron, Inc. | Filler material for dental composites |
US6362251B1 (en) | 1998-10-09 | 2002-03-26 | Degussa-Huls Aktiengesellschaft | Dental material comprising porous glass ceramics, porous glass ceramics, processes and use |
US6417246B1 (en) | 1999-09-21 | 2002-07-09 | Jenerica/Pentron Incorporated | Dental composite materials |
US6232367B1 (en) | 1999-10-07 | 2001-05-15 | Kerr Corporation | Opalescent fillers for dental restorative composites |
US6387981B1 (en) | 1999-10-28 | 2002-05-14 | 3M Innovative Properties Company | Radiopaque dental materials with nano-sized particles |
Cited By (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040086446A1 (en) * | 2001-11-02 | 2004-05-06 | Weitao Jia | Dental resin materials, method of manufacture, and uses thereof |
US7670580B2 (en) * | 2001-11-02 | 2010-03-02 | Pentron Clinical Technologies, Llc | Dental resin materials, method of manufacture, and uses thereof |
US8414297B2 (en) | 2001-12-28 | 2013-04-09 | Randall Rex Calvert | Apparatus and method for root canal obturation |
US20090047634A1 (en) * | 2001-12-28 | 2009-02-19 | Randall Rex Calvert | Apparatus and method for root canal obturation |
US20080145820A1 (en) * | 2003-05-08 | 2008-06-19 | Ajit Karmaker | Method of manufacturing high strength dental restorations |
US7998375B2 (en) | 2003-05-08 | 2011-08-16 | Pentron Clinical Technologies, Llc | Method of manufacturing high strength dental restorations |
US7128573B2 (en) | 2004-02-19 | 2006-10-31 | Pentron Clinical Technologies, Llc | Device for determining shades of dental restorations |
US20050186527A1 (en) * | 2004-02-19 | 2005-08-25 | Pameijer Cornelis H. | Device for determining shades of dental restorations |
US20060058416A1 (en) * | 2004-09-14 | 2006-03-16 | Brandenburg Charles J | Materials leading to improved dental composites and dental composites made therefrom |
US20060058414A1 (en) * | 2004-09-14 | 2006-03-16 | Arthur Samuel D | Materials leading to improved dental composites and dental composites made therefrom |
US20060058418A1 (en) * | 2004-09-14 | 2006-03-16 | Brandenburg Charles J | Materials leading to improved dental composites and dental composites made therefrom |
US7541392B2 (en) * | 2004-09-14 | 2009-06-02 | E.I. Du Pont De Nemours And Company | Materials leading to improved dental composites and dental composites made therefrom |
US20060058415A1 (en) * | 2004-09-14 | 2006-03-16 | Arthur Samuel D | Materials leading to improved dental composites and dental composites made therefrom |
US20060241205A1 (en) * | 2005-04-20 | 2006-10-26 | Weitao Jia | Filler materials for dental composites |
US20070015845A1 (en) * | 2005-07-15 | 2007-01-18 | Pentron Clinical Technologies, Llc | Dental resin composition, method of manufacture, and method of use thereof |
US20090030109A1 (en) * | 2005-11-18 | 2009-01-29 | Hare Robert V | Dental composite restorative material |
US20100323330A1 (en) * | 2005-11-29 | 2010-12-23 | Pentron Clinical Technologies Llc | Tooth Colorant and Whitener, Method of Manufacture, and Method of Use Thereof |
US20100330582A1 (en) * | 2006-06-08 | 2010-12-30 | The University Of Tokushima | Method for production of novel nano silica particle and use of the nano silica particle |
US8455255B2 (en) * | 2006-06-08 | 2013-06-04 | The University Of Tokushima | Method for production of novel nano silica particle and use of the nano silica particle |
US20080206712A1 (en) * | 2007-02-28 | 2008-08-28 | Ultradent Products, Inc. | Resin reinforced zinc polycarboxylate temporary cement compositions and related kits and methods |
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US9907732B2 (en) | 2007-02-28 | 2018-03-06 | Ultradent Products, Inc. | Resin reinforced zinc polycarboxylate temporary cement compositions and related kits and methods |
US8735463B2 (en) | 2007-05-31 | 2014-05-27 | Creighton University | Self-healing dental composites and related methods |
US8342351B2 (en) | 2007-08-03 | 2013-01-01 | Terry J. Hobbs, SR. | Cap for caulking cartridge or similar container |
US11116604B2 (en) | 2008-01-29 | 2021-09-14 | David J. Clark | Dental matrix devices specific to anterior teeth, and injection molded filling techniques and devices |
US20090191505A1 (en) * | 2008-01-29 | 2009-07-30 | Clark David J | Dental Matrix Devices Specific To Anterior Teeth, and Injection Molded Filling Techniques and Devices |
US9414895B2 (en) | 2008-01-29 | 2016-08-16 | David J. Clark | Dental matrix devices specific to anterior teeth, and injection molded filling techniques and devices |
US20100158960A1 (en) * | 2008-12-18 | 2010-06-24 | Dinesh Chandra | Porous polymer coating for tooth whitening |
US9296846B2 (en) | 2008-12-18 | 2016-03-29 | The Trustees Of The University Of Pennsylvania | Porous polymer coating for tooth whitening |
US20100240794A1 (en) * | 2009-03-20 | 2010-09-23 | Shuhua Jin | Dental resin composition, method of manufacture, and method of use thereof |
EP2230286A1 (en) | 2009-03-20 | 2010-09-22 | Pentron Clinical Technologies, LLC | Dental resin composition, method of manufacture, and method uf use thereof |
US8163815B2 (en) | 2009-03-20 | 2012-04-24 | Pentron Clinical Technologies, Llc | Dental resin composition, method of manufacture, and method of use thereof |
EP2253301A1 (en) | 2009-05-18 | 2010-11-24 | Pentron Clinical Technologies, LLC | Pre-treated acid-reactive fillers and their use in dental applications |
WO2010144787A1 (en) | 2009-06-11 | 2010-12-16 | Pentron Clinical Technologies, Llc | Epoxy-containing composition curable by multiple polymerization mechanisms |
US9345647B2 (en) | 2009-06-11 | 2016-05-24 | Pentron Clinical Technologies, Llc | Epoxy-containing dental composition curable by multiple polymerization mechanisms |
EP2537507A2 (en) | 2011-06-20 | 2012-12-26 | Kerr Corporation | Compositions dentaires contenant des fibres raccourcies |
CN110550545A (en) * | 2019-07-15 | 2019-12-10 | 广东中烟工业有限责任公司 | Guide rail and guide wheel device with high wear resistance |
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US7670580B2 (en) | 2010-03-02 |
US20040086446A1 (en) | 2004-05-06 |
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